WO2000051427A1 - Pit-emulsionen - Google Patents
Pit-emulsionen Download PDFInfo
- Publication number
- WO2000051427A1 WO2000051427A1 PCT/EP2000/001311 EP0001311W WO0051427A1 WO 2000051427 A1 WO2000051427 A1 WO 2000051427A1 EP 0001311 W EP0001311 W EP 0001311W WO 0051427 A1 WO0051427 A1 WO 0051427A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- pit emulsions
- emulsions according
- fatty
- water
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Definitions
- the invention is in the field of pesticide formulations and relates to special PIT emulsions with pesticides and selected emulsifiers.
- emulsions of oil-soluble pesticides are often used in the landscape.
- these preparations are not sufficiently stable in storage and, in particular, do not allow the preparation of dilutions or the addition of water-soluble pesticides without breaking the emulsion.
- Another problem is that the activity of the emulsions is not always satisfactory.
- the complex object of the present invention was to provide new crop protection agents with solid and liquid, preferably oil-soluble pesticides, which are simultaneously characterized by a higher storage stability and activity and in particular can be diluted with water without problems and the stable Allow incorporation of additional water-soluble pesticides.
- the invention relates to PIT emulsions containing
- emulsions which contain pesticides together with nonionic emulsifiers, in particular combinations of fatty alcohol ethoxylates and fatty acid partial glycerides, and have been prepared by the phase inversion temperature method (“PIT emulsions”), the complex requirement profile in an excellent manner Way to meet.
- the preparations are distinguished by improved storage stability and higher activity compared to conventional emulsions of the prior art. They can also be easily diluted with water and also allow the subsequent incorporation of water-soluble pesticides.
- the pesticides which are suitable as component (a) are preferably oil-soluble substances. Fungicides, herbicides, insecticides or mixtures thereof can be used. Typical examples of suitable fungicides are azoxystrobin, benalaxyl, carbendazim, chlorothalonil, cupfer, cymoxanil, cyproconazole, diphenoconazole, dinocap, epoxiconazole, fluazinam, fiusilazole, flutriafol, folpel, fosetyl aluminum, hexesaconazole methylax Myclobutanil, Ofurace, Phentinhydroxid, Prochloraz, Pyremethanil, Soufre, Tebucanazol, and Tetraconazol and their mixtures.
- Herbicides which can be used are alachlor, acloniphene, acetochlor, amidosulfuron, aminotriazole, atrazine, bentazone, biphenox, bromoxyl octanoate, bromoxynil, clethodim, chlodinafop-propargyl, chloridazone, chlorosulfuron, chlortoluron, dlomazic, dhamham, cyclomidon, cyclom Difluphenicanil, Dimithenamid, Ethofumesat, Fluazifop, Fluazifop-p-butyl, Fluorochloridon, Fluroxypyr, Glufonsinat, Glyphosat, Haloxyfop-R, loxynil Octanoate, Isoproturon, Isoxaben, Metamitron, Metazachlor, Metolachonuron, Oxolulfon
- insecticides are biphenthrin, carbofuran, carbosulfan, chlorpyriphos-methyl, chlorpy rip os-ethyl I, ß-cyfluthrin, ⁇ -cyhalothrin, cyhexatin, cypermethrin, dicofol, endosulfan, ⁇ -fluvalinate, ⁇ -methrin, ⁇ -methrin, ⁇ -methrin , Pyrimicarb, terbuphos and tebuphenpyrad and mixtures thereof.
- Other suitable pesticides can be found, for example, in the Phytosanitaire 1998 index, 34th edition (ed .: Association de Coordination Technique Agricole, Paris).
- Suitable emulsifiers which form component (b) are nonionic surfactants from at least one of the following groups: (1) Adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the Alkyl group;
- alkyl mono- and oligogiycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
- polystyrene resin e.g. Polyglycerol polyricinoleate or polyglycene poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
- partial esters based on linear, branched, unsaturated or saturated C-6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside -glucoside) and polyglucosides (eg cellulose);
- the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homolog mixtures, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
- Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 2024051 as refatting agents for cosmetic preparations.
- C ⁇ / 18-alkyl mono- and oligoglycosides their preparation and their use as surface-active substances are known for example from US 3,839,318, US 3,707,535, US 3,547,828, DE-OS 1943689, DE-OS 2036472 and DE-A1 3001064 and EP-A1 0077167 . They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
- the glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable.
- the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
- mixtures of at least two nonionic emulsifiers are used, which are in particular (b1) fatty alcohol ethoxylates and (b2) fatty acid partial glycerides.
- the fatty alcohol ethoxylates (component b1) preferably follow the formula (I)
- R 1 is a linear or branched alkyl and / or alkenyl radical having 12 to 24, in particular 16 to 22, carbon atoms and n is a number from 1 to 30, in particular 10 to 20.
- Typical examples are the addition products of an average of 10 to 20 mol ethylene oxide onto cetyl alcohol, stearyl alcohol, isostearyl alcohol, cetearyl alcohol and behenyl alcohol.
- the fatty acid partial glycerides that is to say monoglycerides, diglycerides and their technical mixtures, which may still contain small amounts of triglycerides due to the production process and which form the sub-component (b2), generally follow formula (II),
- R 2 CO for a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18 carbon atoms
- R 3 and R 4 independently of one another for R 2 CO or OH and the sum (m + p + q ) stands for 0 or numbers from 1 to 100, preferably 5 to 25, with the proviso that at least one of the two radicals R 3 and R 4 is OH.
- Typical examples are mono- and / or diglycerides based on caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linoleic acid, linoleic acid Elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
- non-polar solvents for example, mineral oils, fatty acid lower alkyl esters, such as e.g. the C ⁇ -C -, i.e.
- methyl, ethyl, propyl and / or butyl ester of caproic acid caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linoleic acid, linoleic acid, Elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures in question.
- Vegetable triglycerides such as coconut oil, palm oil, palm kernel oil, sunflower oil, olive oil and the like are also suitable.
- the PIT emulsions according to the invention contain
- the amounts given with water and, if appropriate, other conventional auxiliaries and additives are 100% by weight.
- the water content of the emulsions is on average 30 to 90 and in particular 40 to 60% by weight, the droplet size is 0.01 to 1, preferably 0.1 to 0.5 ⁇ m.
- the invention further relates to a process for the preparation of pesticide emulsions in which the oil-soluble pesticides are homogenized together with the nonionic emulsifiers and 40 to 60% by weight, based on the final formulation, of water until heated above the phase inversion temperature, adding the remaining amount of water, allowing the emulsion to cool and then optionally diluting it with a further amount of water to the application concentration and / or adding further water-soluble pesticides.
- Emulsions 1 to 3 according to the invention were prepared by the PIT process, the comparison emulsions V1 and V2 by conventional hot processes. The emulsions were then stored for 1 week at 20 ° C. or 4 weeks at 40 ° C. and examined for their stability; (++) means stable, (+) slight turbidity and (-) phase separation. Furthermore, the emulsions were diluted with water to an active substance content of 1% by weight at 20.degree. C. and the stability was assessed in the same way. The results are summarized in Table 1.
- the PIT emulsions according to the invention proved to be stable both when stored at temperature and when diluted, while the comparison emulsions did not allow temperature stress or the addition of water.
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Colloid Chemistry (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00916844A EP1162881B1 (de) | 1999-02-27 | 2000-02-18 | Pit-emulsionen |
DE50006074T DE50006074D1 (de) | 1999-02-27 | 2000-02-18 | Pit-emulsionen |
CA002362506A CA2362506A1 (en) | 1999-02-27 | 2000-02-18 | Pit emulsions |
US09/914,431 US6716443B1 (en) | 1999-02-27 | 2000-02-18 | PIT emulsions |
BR0008445-0A BR0008445A (pt) | 1999-02-27 | 2000-02-18 | Emulsões pit |
AT00916844T ATE264055T1 (de) | 1999-02-27 | 2000-02-18 | Pit-emulsionen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19908559.5 | 1999-02-27 | ||
DE19908559A DE19908559A1 (de) | 1999-02-27 | 1999-02-27 | PIT-Emulsionen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000051427A1 true WO2000051427A1 (de) | 2000-09-08 |
Family
ID=7899093
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/001311 WO2000051427A1 (de) | 1999-02-27 | 2000-02-18 | Pit-emulsionen |
Country Status (9)
Country | Link |
---|---|
US (1) | US6716443B1 (de) |
EP (1) | EP1162881B1 (de) |
AR (1) | AR022773A1 (de) |
AT (1) | ATE264055T1 (de) |
BR (1) | BR0008445A (de) |
CA (1) | CA2362506A1 (de) |
DE (2) | DE19908559A1 (de) |
ES (1) | ES2219327T3 (de) |
WO (1) | WO2000051427A1 (de) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001032019A1 (de) * | 1999-11-05 | 2001-05-10 | Cognis Iberia, S.L. | Agrochemische emulsionen |
WO2001050861A1 (de) * | 2000-01-07 | 2001-07-19 | Cognis Deutschland Gmbh & Co. Kg | Wässriges herbizides mittel |
WO2002049432A1 (de) * | 2000-12-20 | 2002-06-27 | Bayer Cropscience Gmbh | Herbizide mittel |
US6759371B2 (en) | 2000-01-07 | 2004-07-06 | Cognis Deutschland Gmbh & Co. Kg | Bromoxynil component-containing herbicidal preparations with enhanced penetration and methods of using same |
US6764979B2 (en) * | 2000-04-12 | 2004-07-20 | Cognis Deutschland Gmbh & Co. Kg | Aqueous herbicidal agent |
CN100399901C (zh) * | 2001-04-11 | 2008-07-09 | 拜尔农作物科学股份公司 | 脂肪族醇乙氧基化物作为渗透剂的用途 |
WO2014140484A1 (fr) | 2013-03-14 | 2014-09-18 | Agronutrition | Utilisations d'esters carboniques de glycérol acylés en agriculture |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10025671B4 (de) * | 2000-05-24 | 2006-07-27 | Cognis Ip Management Gmbh | Emulgatoren |
CA2578594C (en) * | 2004-08-31 | 2012-04-17 | Connetics Australia Pty Ltd | Microemulsion & sub-micron emulsion process & compositions |
EP1861067A2 (de) * | 2005-03-09 | 2007-12-05 | Combe Incorporated | Stabile mischemulsionen mit halbfesten dispersionen aus mindestens zwei separaten und eindeutig unterschiedlichen partikelgrössenbereichen |
CA2600288A1 (en) * | 2005-09-19 | 2007-04-12 | Combe Incorporated | Stable emulsion systems with high salt tolerance |
DE102007018983A1 (de) * | 2007-04-21 | 2008-10-23 | Cognis Ip Management Gmbh | Agrochemische Zubereitungen |
WO2010052178A1 (de) * | 2008-11-07 | 2010-05-14 | Basf Se | Agrochemische formulierung mit drei lösungsmitteln |
FR3025698B1 (fr) * | 2014-09-12 | 2017-11-24 | Agronutrition | Nouvelles utilisations d'esters carboniques de glycerol en agriculture |
US11007161B1 (en) | 2014-12-31 | 2021-05-18 | Eric Morrison | Ibuprofen nanoparticle carriers encapsulated with hermatic surfactant films |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993014630A1 (en) * | 1992-01-31 | 1993-08-05 | Nc Development, Inc. | Pesticidal pre-treatment of wood by microemulsion, micellar or molecular solution |
EP0589334A1 (de) * | 1992-09-24 | 1994-03-30 | Hoechst Schering AgrEvo GmbH | Neue konzentrierte wässrige Emulsionen von Neophanen und Azaneophanen |
DE4337041A1 (de) * | 1993-10-29 | 1995-05-04 | Henkel Kgaa | Verfahren zur Herstellung in Öl-in-Wasser-Emulsionen |
WO1998009721A2 (de) * | 1996-09-02 | 1998-03-12 | Henkel Kommanditgesellschaft Auf Aktien | Emulgatormischungen und deren verwendung zur herstellung von pit-emulsionen |
WO1998032413A1 (de) * | 1997-01-29 | 1998-07-30 | Henkel Kommanditgesellschaft Auf Aktien | Kosmetische pit-emulsionen |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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DE1165574B (de) | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Verfahren zur Herstellung von als Emulgiermittel fuer Salbengrundlagen dienenden Mischestern |
US3547828A (en) | 1968-09-03 | 1970-12-15 | Rohm & Haas | Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols |
US3707535A (en) | 1969-07-24 | 1972-12-26 | Atlas Chem Ind | Process for preparing mono- and polyglycosides |
US3772269A (en) | 1969-07-24 | 1973-11-13 | Ici America Inc | Glycoside compositions and process for the preparation thereof |
DE2024051C3 (de) | 1970-05-16 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Verwendung der Veresterungsprodukte von Glycerin-Äthylenoxid-Addukten mit Fettsäuren als Rückfettungsmittel in kosmetischen Zubereitungen |
US3839318A (en) | 1970-09-27 | 1974-10-01 | Rohm & Haas | Process for preparation of alkyl glucosides and alkyl oligosaccharides |
DE3001064A1 (de) | 1980-01-12 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur reinigung von alkylglycosiden durch destillative abtennung nicht umgesetzter alkohole |
DE3266210D1 (en) | 1981-10-08 | 1985-10-17 | Rohm & Haas France | A process for preparing surface-active glycosides and the use of the glycosides in cosmetic, pharmaceutical and household products |
CA1301642C (en) * | 1987-03-30 | 1992-05-26 | Howard Bernard Dawson | Chemical formulations |
GB8822936D0 (en) * | 1988-09-30 | 1988-11-09 | Nc Dev Inc | Pesticidal control |
ES2016692A6 (es) * | 1989-04-12 | 1990-11-16 | Lainco S A | Una composicion pesticida ecologica que no contamina ell medio ambiente, procedimiento para su obtencion y empleo de la misma para combatir parasitos daninos para las plantas. |
-
1999
- 1999-02-27 DE DE19908559A patent/DE19908559A1/de not_active Withdrawn
-
2000
- 2000-02-18 ES ES00916844T patent/ES2219327T3/es not_active Expired - Lifetime
- 2000-02-18 AT AT00916844T patent/ATE264055T1/de not_active IP Right Cessation
- 2000-02-18 WO PCT/EP2000/001311 patent/WO2000051427A1/de active IP Right Grant
- 2000-02-18 DE DE50006074T patent/DE50006074D1/de not_active Expired - Lifetime
- 2000-02-18 BR BR0008445-0A patent/BR0008445A/pt not_active IP Right Cessation
- 2000-02-18 EP EP00916844A patent/EP1162881B1/de not_active Expired - Lifetime
- 2000-02-18 CA CA002362506A patent/CA2362506A1/en not_active Abandoned
- 2000-02-18 US US09/914,431 patent/US6716443B1/en not_active Expired - Fee Related
- 2000-02-25 AR ARP000100848A patent/AR022773A1/es unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993014630A1 (en) * | 1992-01-31 | 1993-08-05 | Nc Development, Inc. | Pesticidal pre-treatment of wood by microemulsion, micellar or molecular solution |
EP0589334A1 (de) * | 1992-09-24 | 1994-03-30 | Hoechst Schering AgrEvo GmbH | Neue konzentrierte wässrige Emulsionen von Neophanen und Azaneophanen |
DE4337041A1 (de) * | 1993-10-29 | 1995-05-04 | Henkel Kgaa | Verfahren zur Herstellung in Öl-in-Wasser-Emulsionen |
WO1998009721A2 (de) * | 1996-09-02 | 1998-03-12 | Henkel Kommanditgesellschaft Auf Aktien | Emulgatormischungen und deren verwendung zur herstellung von pit-emulsionen |
WO1998032413A1 (de) * | 1997-01-29 | 1998-07-30 | Henkel Kommanditgesellschaft Auf Aktien | Kosmetische pit-emulsionen |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001032019A1 (de) * | 1999-11-05 | 2001-05-10 | Cognis Iberia, S.L. | Agrochemische emulsionen |
WO2001050861A1 (de) * | 2000-01-07 | 2001-07-19 | Cognis Deutschland Gmbh & Co. Kg | Wässriges herbizides mittel |
US6759371B2 (en) | 2000-01-07 | 2004-07-06 | Cognis Deutschland Gmbh & Co. Kg | Bromoxynil component-containing herbicidal preparations with enhanced penetration and methods of using same |
US6764979B2 (en) * | 2000-04-12 | 2004-07-20 | Cognis Deutschland Gmbh & Co. Kg | Aqueous herbicidal agent |
WO2002049432A1 (de) * | 2000-12-20 | 2002-06-27 | Bayer Cropscience Gmbh | Herbizide mittel |
US6693063B2 (en) | 2000-12-20 | 2004-02-17 | Aventis Cropscience Gmbh | Herbicidal composition |
CN100399901C (zh) * | 2001-04-11 | 2008-07-09 | 拜尔农作物科学股份公司 | 脂肪族醇乙氧基化物作为渗透剂的用途 |
WO2014140484A1 (fr) | 2013-03-14 | 2014-09-18 | Agronutrition | Utilisations d'esters carboniques de glycérol acylés en agriculture |
FR3003130A1 (fr) * | 2013-03-14 | 2014-09-19 | Agronutrition | Utilisations d'esters carboniques de glycerol en agriculture |
US9790135B2 (en) | 2013-03-14 | 2017-10-17 | Agronutrition | Use of acylated carbonic esters of glycerol in agriculture |
Also Published As
Publication number | Publication date |
---|---|
EP1162881A1 (de) | 2001-12-19 |
AR022773A1 (es) | 2002-09-04 |
CA2362506A1 (en) | 2000-09-08 |
ES2219327T3 (es) | 2004-12-01 |
BR0008445A (pt) | 2002-01-15 |
ATE264055T1 (de) | 2004-04-15 |
EP1162881B1 (de) | 2004-04-14 |
DE19908559A1 (de) | 2000-09-07 |
DE50006074D1 (de) | 2004-05-19 |
US6716443B1 (en) | 2004-04-06 |
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